Is the CHIRP software easy to learn?
It's been a while since I last used it, but I don't recall it being that difficult. BTW, it is free-ware (or donor supported).
You need a special usb cable that has the two plugs that match up with side of radio, so you'd have to buy one of these --> Amazon.com: Baofeng USB Programming Cable PL2303 for Baofeng UV-5R,BF-F8HP, BF-888S,UV-82HP,GT-3 Handheld ham Radio transceiver Ham Two Way Radio with Driver CD: Industrial & Scientific
You can download CHIRP here --> Download - CHIRP